(S)-methyl 2-(3-hydroxypyrrolidin-1-yl)-5-(trifluoromethyl)benzoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-methyl 2-(3-hydroxypyrrolidin-1-yl)-5-(trifluoromethyl)benzoate
• 英文别名: (S)-Methyl 2-(3-hydroxypyrrolidin-1-YL)-5-(trifluoromethyl)benzoate；methyl 2-[(3S)-3-hydroxypyrrolidin-1-yl]-5-(trifluoromethyl)benzoate
• 化学式: C₁₃H₁₄F₃NO₃
• 分子量: 289.254
• InChiKey: UDETUOBIPKELFP-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(3-hydroxypyrrolidin-1-yl)-5-(trifluoromethyl)benzoate 在 palladium 10% on activated carbon 、 水 、 氢气 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 61.0h， 生成 (S)-2-(3-(2-hydroxyethoxy)pyrrolidin-1-yl)-5-(trifluoromethyl)benzoic acid
  参考文献：
  名称：

  Discovery of XEN445: A potent and selective endothelial lipase inhibitor raises plasma HDL-cholesterol concentration in mice

  摘要：

  Endothelial lipase (EL) activity has been implicated in HDL metabolism and in atherosclerotic plaque development; inhibitors are proposed to be efficacious in the treatment of dyslipidemia related cardiovascular disease. We describe here the discovery of a novel class of anthranilic acids EL inhibitors. XEN445 (compound 13) was identified as a potent and selective EL inhibitor, that showed good ADME and PK properties, and demonstrated in vivo efficacy in raising plasma HDLc concentrations in mice. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.023
• 作为产物：
  描述：

  2-氟-5-三氟甲基苯甲酸 在 N-甲基吗啉 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 (S)-methyl 2-(3-hydroxypyrrolidin-1-yl)-5-(trifluoromethyl)benzoate
  参考文献：
  名称：

  Discovery of XEN445: A potent and selective endothelial lipase inhibitor raises plasma HDL-cholesterol concentration in mice

  摘要：

  Endothelial lipase (EL) activity has been implicated in HDL metabolism and in atherosclerotic plaque development; inhibitors are proposed to be efficacious in the treatment of dyslipidemia related cardiovascular disease. We describe here the discovery of a novel class of anthranilic acids EL inhibitors. XEN445 (compound 13) was identified as a potent and selective EL inhibitor, that showed good ADME and PK properties, and demonstrated in vivo efficacy in raising plasma HDLc concentrations in mice. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.023

文献信息

• Discovery of XEN445: A potent and selective endothelial lipase inhibitor raises plasma HDL-cholesterol concentration in mice
  作者：Shaoyi Sun、Richard Dean、Qi Jia、Alla Zenova、Jing Zhong、Celene Grayson、Clark Xie、Andrea Lindgren、Pritpaul Samra、Luis Sojo、Margaret van Heek、Linus Lin、David Percival、Jian-min Fu、Michael D. Winther、Zaihui Zhang

  DOI：10.1016/j.bmc.2013.10.023

  日期：2013.12

  Endothelial lipase (EL) activity has been implicated in HDL metabolism and in atherosclerotic plaque development; inhibitors are proposed to be efficacious in the treatment of dyslipidemia related cardiovascular disease. We describe here the discovery of a novel class of anthranilic acids EL inhibitors. XEN445 (compound 13) was identified as a potent and selective EL inhibitor, that showed good ADME and PK properties, and demonstrated in vivo efficacy in raising plasma HDLc concentrations in mice. (C) 2013 Elsevier Ltd. All rights reserved.